However, while there is a ton of data on short term rentals I am having a hard time finding good research on the luxury segment of the market.

Perhaps the segment below the high-end.

He has a book on Amazon, "Ask", and it's a great read. https://www.amazon.com/Ask-Cou...Glenn Livingston I think, has figured out he can make a bundle of money by using his skills to go after a huge market segment, instead of teaching his skills as he used to or offering them as a service.A good question to ask, is if my goal is X, what do I need to do to achieve X in 5 years.

As an example, I can see in my regions that most of the listings on page one are either low-cost superhost or new listings: two segments that AirBnB has a vested interest in promoting on their platform. 

And, you will need multiple reliable tenants over the years you hold the property.The best way to consistently have a reliable tenant in your property is to select a tenant segment with a high concentration of reliable tenants.

Besides usual skill set of construction, real estate and managerial knowledge and ability requires local market knowledge and property segment knowledge. 5.

Looking at a three or four year segment of time can be powerfully misleading.    

Smaller cities may be too dependent on a single employer or market segment, which can lead to instability over the long run.Both state and metro populations are increasing.

The city I live in (Rome) is extremely competitive in the property management segment so growth will take time along with finding some competitive edge.

Baltimore has always been a very segmented city by neighborhood.